


Agent Winchester

by Anonymous



Category: Supernatural
Genre: Accidental Voyeurism, Alternate Universe - College/University, Angst with a Happy Ending, College Student Castiel (Supernatural), FBI Agent Dean Winchester, Kinda, M/M, based on the memes, offscreen sex, unrealistic probably
Language: English
Status: Completed
Published: 2019-06-04
Updated: 2019-06-04
Packaged: 2020-04-07 13:15:00
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,503
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19085788
Author URL: https://archiveofourown.org/
Summary: Dean is the FBI agent assigned to spy on Castiel.  He accidentally sees too much one night when watching Cas through his computer camera.





	Agent Winchester

**Author's Note:**

> Kinda based on those memes. kinda a manifestation of my fears of my research getting me flagged. :)

It was supposed to be Dean’s last night of observation on Novak, Castiel. He was meant to finish his observations tonight, and do the write up of the report tomorrow. He’d had everything all planned out, and he was ready to finish this case. He’d been watching the boy for about a week now, and realized this was just another case of someone’s innocent (but weird) google searches getting flagged. He’d discovered that Castiel was a grad student, and his research required him to make increasingly weirder searches. 

To be honest, Dean was ready for this case to be over. When he’d first saw Castiel, he’d thought he was attractive, but as the week progressed, his feelings toward the man had grown. Everything about him was perfect and endearing. Dean liked watching the grumpy scowl slowly leave his face as he drank his morning coffee and checked his email. He liked how Castiel’s tongue stuck out slightly when he was particularly confused about what he was reading for class. And the way he’d get lost scrolling through social media and giggling at memes when he took study breaks. Dean found himself wanting to get to know this man more, and knew it was best if he finished the case so he could have a break. 

Dean was thinking about closing feed and going home for the night. Castiel had been sprawled across the couch watching reruns of Parks and Rec since he’d stopped studying at promptly 9 o’clock like he did every night. Dean was watching him through his computer, which he’d left open on the table when he’d finished studying. A few hours had passed, and Castiel had slumped so far down the couch that Dean couldn’t see his face very well, and he wasn’t even sure if the man was awake. Dean hated how easy he made it to spy on him, but he’d been able to complete his job quickly because of it. 

Dean’s mouse was hovering over the button that would close the feed when Castiel’s twin brother returned home from work. According to the file Dean had received, his name was James, but he’d never heard Castiel call him anything but Jimmy or Jim. When he walked through the door, Castiel’s face lit up, and he immediately opened his arms for him to crawl into. That’s a little weird Dean thought. He’d never cuddled with Sam like that. Sure sometimes they sat close, or maybe one would sit with an arm around the other if they were having a bad day or something. But they’d never cuddled like this. 

Castiel and Jimmy were plastered together from head to toe. Both were facing the tv, Castiel had his arms wrapped around Jimmy from behind, and Jimmy was holding Castiel’s hands where they rested on his stomach. Maybe it was a twin thing. Or maybe Castiel had missed spending time with Jimmy. Every time Dean had seen Jimmy on the feed, he’d had his head buried in notes and textbooks. Maybe Castiel was just happy to spend time with his brother now that the semester had ended. 

As Dean was trying to reason with himself, Jimmy turned around in Castiel’s arms so that they were face to face, noses almost touching. Dean’s thoughts completely cut off as his eyes widened and he leaned toward the screen. He watched Castiel brush Jimmy’s hair out of his face before resting his hand on his check. Dean looked away from the screen trying to mentally prepare himself for he thought was about to happen. When he let himself look at the screen again, he let out a small gasp. Jimmy had propped himself up on his elbow so he was leaning over Castiel slightly, and the two men were kissing. 

Dean didn’t think he’d ever gotten so hard so quickly. He was already aching to be touched, and he’d only watched them kiss for a few seconds. He instinctively started to touch himself, but stopped when he realized how creepy he was being. His hands gripped the table so he couldn’t touch, but he couldn’t quite bring himself to close the feed, eyes glued to their slow moving mouths.

Dean watched as things on the screen became more heated. Both men had lost their shirts, and were slowly thrusting against each other. Dean’s knuckles were white from holding the table so tightly. His jaw dropped as Jimmy pulled Castiel into a sitting position, and slid to floor on his knees. He watched Jimmy kiss Castiel’s chest and stomach, but as soon as Jimmy reached for Castiel’s pants zipper, he panicked, and closed the feed. 

Dean shoved his chair back from his desk. He leaned his head back to look at the ceiling, and took a few deep breaths. He couldn’t believe he just did that. He knew this man wasn’t doing anything wrong, so he had no reason to watch the feed after they started kissing. Dean had to close this case tonight. 

Dean sat up straight, and rubbed his eyes with his fists. He was tired, but his guilt was going to force him to finish up his paperwork tonight so he had no excuse to even check on Castiel tomorrow.   
He quickly turned back to his desk to do one last search of Castiel’s files. The only thing he seemed to have on his computer were thousands of photos and a flash drive full of school assignments. Dean couldn’t find anything troubling, and his school research matched the searches that got him flagged in the first place. Opening Castiel’s file, Dean got to work on adding his final notes so he could finish this case, and never think about Castiel or Jimmy again. 

—————

One week had passed since the incident, and Dean had jerked off to thoughts of the twins every night since. He felt guilty about it every time, but he just can’t stop thinking about them, about what he would’ve seen if he’d kept watching. He’d tried watching porn, but it didn’t help so tonight he’d decided to go to bar and try to bring someone home. If anything will make him forget, it’s mindless sex with a stranger. 

When Dean arrived at the bar, he immediately claimed his favorite stool in the corner. He liked this spot because it allowed him to remain in the background until he wanted to be seen. He could have a few drinks and consider his options before making a move on someone. As he sat down, he took a quick look around the room. Nobody caught his eye, but it was still early so he wasn’t worried. Settling into his seat, Dean waved the bar tender over, and ordered a beer. 

Several beers later, Dean was feeling somewhere between buzzed and drunk. He could think clearly if he really tried, but everything felt kinda fuzzy. He’d been checking the crowd periodically, but no one was catching his eye. Deciding this was a bad idea, he raised his hand to wave the bartender over so he could pay his tab, but before Dean could get her attention, he dropped his hand, distracted by a man sitting down on the stool next to him. 

“You hiding in this corner on purpose?” 

Dean turned to answer the man, but when he saw who was sitting next to him, his jaw dropped and he froze unable to speak. One of the Novak twins was sitting next to him with a smirk on his face. When Dean failed to respond, he tried again. “Listen, I know I look good, but I’ve never quite gotten this reaction before.” 

His words finally caused Dean to snap out of his thoughts. He held his hand out for the man to shake while he introduced himself. “H- hey, I’m Dean. Sorry about that you’re just really hot.” 

Color flooded Dean’s cheeks. He couldn’t believe he’d just said that. He wanted the ground to swallow him whole. The man didn’t seem to mind, however, because he laughed before introducing himself. “Hello, Dean. I’m Castiel, but everyone calls me Cas.”

Dean smiled at Cas, but didn’t know what to say. He felt too awkward around this man to easily make conversation. If Cas only knew what Dean knew. Sensing Dean’s hesitancy, Cas leaned out of Dean’s space. “I can go away if you want. It was bold of me to assume you wanted company when you’re sitting over here in the corner alone. Don’t feel obligated to entertain me, Dean.” 

Dean felt even more guilty because Cas was being so kind and considerate of his feelings, and Dean has already betrayed his trust in a huge way. Pushing through his guilt, Dean smiled at him again. “No it’s okay. Please stay.” Dean wasn’t happy with how whiny his voice sounded. 

Cas smiled back at Dean seeming please that he wanted his company. “How about you come back to my table with me? It’s just me and my brother having a few beers.”

Dean hesitated at the thought of him, Jimmy, and Cas in a booth in the dark bar together. He didn’t know how to act around Cas by himself, he certainly wouldn’t know how to act around the two of them together. 

“Are you sure you’re okay, Dean?” Cast asked, pulling Dean out of his thoughts once more. 

Dean offered a reassuring smile as he stood up. “I’m great, Cas. Let’s go back to your table. I wanna meet your brother.”

Cas led Dean back to the table, a circular booth in the opposite corner, and introduced him to Jimmy. Dean managed to handle himself a little better this time, only blushing slightly as he faked being shocked about them being twins. Jimmy ordered more beers, and the three men talked and laughed and learned about one another. 

After another beer, Cas and Jimmy must’ve been feeling more confidant because they slowly started scooting closer to Dean. At first he thought he was imagining it, but soon they had him completely box in. Jimmy had casually put a hand on his thigh, and Cas had his arm half way around his shoulder and was playing with the short hairs at the back of his neck. Dean was starting to feel sweaty and desperate. He knew if Jimmy moved his hand up just a couple inches, he’d be able to feel how incredibly hard he’d already become. 

Jimmy leaned in his head toward Dean’s, until his lips were barely brushing his ear. “Do you wanna come home with us, Dean?”

Dean’s fingers tightened around his beer bottle so much he was afraid it would shatter in his hands. His brain seemed to have stopped working altogether at this point because instead of answering Jimmy’s question, he blurted out his own question that he’d been agonizing over since he’d first seen them together on the feed. “Are you two like... together?”

He watched them share a look, and was momentarily afraid he’d overstepped. Both of them took their hands off of Dean and scooted away slightly causing Dean to whine out. Cas smiler softly at that, but made no move to return to his previous position. 

The twins shared another look before Cas started speaking. “We aren’t together, but we sometimes try to hook up together because it’s easier. Everyone wants a little taboo for the night and to forget about it in the morning.” 

“Cassie, you make it sound so weird. Yeah it makes it easier some nights. But I’m hot as fuck which makes Cas hot as fuck by default. It’s not like it’s a chore to have threesomes with my brother either,” Jimmy added with a smirk. 

Dean looked back and forth between the two men. He wasn’t sure what to believe. He’d seen them together before, but maybe it was a one time thing. Maybe they both wanted a hook up but didn’t want to go out, if they’ve already done this together that wouldn’t be too weird. Or maybe they’re just lying because they don’t want Dean to be weird about it. Dean can’t really be mad at them if they’re lying, his lie is a thousand times worse than this really. 

Taking a deep breath and burying his guilt, Dean finally gave them their answer by pulling Cas into a deep kiss. He heard Jimmy’s delighted gasp next to them, but couldn’t pull away. Jimmy began scooting toward the edge of the booth. “I’m gonna go pay our tabs. I’ll meet you both in the car. I’ve only had one beer so I’ll drive.”

Dean and Cas slowly made their way to the car. They could barely separate long enough to watch where they were walking, but Dean made sure to pay Baby on his way by, and let her know he’d come back for her tomorrow. By the time Jimmy got to the car, Cas was in Dean’s lap in the backseat slowly grinding on him. 

When Jimmy opened the door, he looked into the back seat longingly before starting the car. Turning back to them once more he said, “Alright, I don’t care what you do on the way home, but I need butts in seats.”

With an exasperated sigh and an eye roll, Cas rolled off of Dean into his own seat, and put his seatbelt on. The two men continued kissing the whole way back to the twins’ house with Jimmy turning around to watch at every stoplight. 

By the time they arrived, Dean’s dick was so hard he was worried it might fall off, but his guilt was also clawing its way back to the surface making it difficult for him to relax. They slowly made it inside and to the couch. Cas and Jimmy shoved Dean down, and sat on each side of him. Jimmy pulled Dean’s face toward his so he could kiss him finally, but as soon as their lips met, Dean pulled himself away, and put his hands over his face. 

Cas sat his hand on Dean’s shoulder. “Dean are you sure you’re okay? We can stop anytime, neither of us will be mad or upset.” 

Dean didn’t remove his hands from his face, but he tried to make them feel better. “I’m fine I swear. I just need a minute.”

Jimmy shared a look with Cas then hesitantly tried to pry Dean’s hands away from his face. When he was successful he cautiously asked, “Have you ever been with a man before?”

Dean took the opportunity that was just thrown to him. If he said yes, it would help to explain away his nerves. It wouldn’t even be a lie. Even if he was being a bit deceptive about what was wrong, he really hadn’t been with a man before. He knows he likes men, but he’d never done anything more than kissing with men. 

“I... No, I haven’t. I’m sorry that’s kinda lame. I’m just a little nervous,” Dean whispered nervously. 

Each twin grabbed one of Dean’s hands. “You don’t have to do anything you don’t want, Dean. We’d love for your first time to be with a man to be with us, but if it’s too much right now that’s okay. A little bit of nerves are normal and okay, but you’re really nervous. Are you sure you’re ready?”

Dean really didn’t want to lose this opportunity. Jimmy and Cas were both so hot, and he knew he’d regret it if he fucked this up. Deciding they’d done enough talking, Dean pulled Jimmy’s mouth back to his. 

Kissing Jimmy made it hard to concentrate on anything else so Dean was only vaguely aware that Cas was moving around. He jumped a little when he felt Cas’ hands at the zipper of his jeans, but tried to stay calm so they didn’t stop again. Cas slowly unbuttoned his pants and pulled down his zipper, but before he could pull his pants down, Dean’s calm flew out the window. 

Dean jumped up shoving both men off of him leaving both men shocked on the couch. He started pacing in small space between their coffee table and tv. “Okay, I lied a little bit, and everything’s not fine. I have something I have to tell you before we can do this.” 

Dean stopped talking, but continued to pace anxiously. The twins seemed to know they should let him work through it on his own because they both waited patiently for him to speak. Dean finally stopped pacing, and looked at Cas and Jimmy. “I’m gonna lose my job,” he muttered. 

“I don’t really know how to say this in a good way so I’m just gonna go for it. First, I didn’t lie about this being my first time with a man. That was true, and it’s part of the reason I’m so nervous. Second, meeting you tonight really was a coincidence. When I tell you what I have to tell you, you probably won’t believe me, but I had no intention of seeking you out.”

Dean trailed off again. He knew he said he was gonna just go for it, but really how do you tell someone you were a federal agent assigned to spy on them until a week ago. Cas hesitantly spoke up, “It’s okay, Dean. You can tell us whatever it is. I’m sure it’ll be okay.” 

Dean looked skeptical, but started talking. “I’m an FBI agent, and a few weeks ago I was assigned to spy on Cas after some of his research caused him to get flagged. It was clear that you’re both just college students, and that you weren’t doing anything wrong or illegal. I had one more day of observation, and then I was going to finish my report. The last day was the day after Jimmy’s big exam, and before I closed the feed for the night, I saw you two kissing. I swear I stopped it before anything more could happen. I’ll admit you’ve both been on my mind this week, but I genuinely had no intentions to find you or for any of this to happen.”

Dean finally stopped talking, and waited anxiously for either of them to respond. After a few moments of silence, it seemed clear to Dean that he should leave. “I’ll just go then. Again, I’m so sorry. I enjoyed our time tonight and I’m sorry if I’ve made you feel uncomfortable.” Dean walked toward the door, and started putting his shoes on. 

“Wait! Please don’t go!” Dean hesitantly turned around at the sound of Cas’ voice. 

“I’m not going to say I’m not incredibly alarmed, but Dean this isn’t on you. You were assigned that job by someone else who decided I needed to be spied on. You weren’t honest at first, but it’s clear you didn’t feel right about it, and you told us before anything serious happened.” 

As Cas was talking, Jimmy held his hand out gesturing for Dean to come sit back down. Surprised by there positive reaction, Dean slowly made his way back to his spot on the couch. 

“I’m really sorry about all of this,” he whispered. 

Cas leaned his head on Dean’s shoulder while Jimmy sat sideways beside the pair with his knees pulled up this his chest leaning on Dean slightly. 

“We’re sorry we lied too. We actually are together, but a lot of people get weird if they think it’s more than a one time thing.”

Dean frowned slightly. “I’m sorry you’ve had to deal with people like that. For what it’s worth, I don’t think it’s weird. I think it’s different, but you love who you love ya know. It’s not hurting anyone.”

Cas pulled away from Dean’s shoulder to get a better look at him. He stared at his face intently like he was searching for something. His eyes flickered briefly to Jimmy’s then back to Dean. 

“We have a question for you. This may sound a bit strange, but would you like to go on a date with us?” 

“A date?” Dean looked confused and hopeful. How did this complete disaster of a situation turn into these two men asking for a date? 

Dean turned toward Jimmy when he started explaining. “Yeah, a date. It’ll have to be lowkey because we’re very obviously brothers and theirs no real way to hide that, but Cassie and I go on dates all the time.”

Dean looked back and forth between the two men as a smile spread across his face. “Okay, let’s go on a date.” 

All the ups and downs of the night had ruined any prospect of sex, but they didn’t seem the care. The three men cuddled on the couch talking softly until Dean started to doze off. Cas and Jimmy gently helped him stand up, and led him to their bedroom. As the twins helped Dean change into more comfortable sleep clothes and curled up under the blankets with him, he found himself hoping this would turn into something real.


End file.
